Dichlorodiphenyldichloroethylene

Dichlorodiphenyldichloroethylene (DDE) is a
Dichlorodiphenyldichloroethylene
chemical compound formed by the loss of hydrogen
chloride (dehydrohalogenation) from DDT, of which it is
one of the more common breakdown products.[1] Due to
DDT's massive prevalence in society and agriculture
during the mid 20th century, DDT and DDE are still
widely seen in animal tissue samples.[2] DDE is
particularly dangerous because it is fat-soluble like other
organochlorines; thus, it is rarely excreted from the body,
and concentrations tend to increase throughout life. The
major exception is the excretion of DDE in breast milk,
which transfers a substantial portion of the mother's DDE
burden to the young animal or child.[3] Along with
accumulation over an organism's lifetime, this stability
leads to bioaccumulation in the environment, which Names
amplifies DDE's negative effects. Preferred IUPAC name
1,1′-(2,2-Dichloroethene-1,1-diyl)bis(4-
Synthesis chlorobenzene)
Other names
DDE is created by dehydrohalogenation of DDT. The loss
Dichlorodiphenyldichloroethylene
of HCl results in a double bond on the central (previously
quaternary) carbon atoms. 1,1-Dichloro-2,2-bis(4-
chlorophenyl)ethene

Identifiers
CAS Number 72-55-9 (https://commonc
hemistry.cas.org/detail?ca
s_rn=72-55-9)
Degradation of DDT to form DDE by an elimination of
HCl 3D model Interactive image (https://
(JSmol) chemapps.stolaf.edu/jmo
l/jmol.php?model=Clc2cc
Toxicity c%28%5CC%28%3DC%
DDE has been shown to be toxic to rats at 79.6 mg/kg.[4] 28%2FCl%29Cl%29c1cc
DDE and its parent, DDT, are reproductive toxicants for c%28Cl%29cc1%29cc2)
certain birds species, and major reasons for the decline of Abbreviations p,p'-DDE
the bald eagle,[5] brown pelican[6] peregrine falcon, and
ChEBI CHEBI:16598 (https://ww
osprey.[7] These compounds cause egg shell thinning in
w.ebi.ac.uk/chebi/searchI
susceptible species, which leads to the birds' crushing their
d.do?chebiId=16598)
eggs instead of incubating them, due to the latter's lack of
resistance.[8] Birds of prey, waterfowl, and song birds are ChEMBL ChEMBL363207 (https://
www.ebi.ac.uk/chembldb/i
more susceptible to eggshell thinning than chickens and ndex.php/compound/insp
related species, and DDE appears to be more potent than ect/ChEMBL363207)
DDT.[7] ChemSpider 2927 (https://www.chems
pider.com/Chemical-Struc
A research shows that an elevated blood levels of DDEs
ture.2927.html)
(also of other toxic molecule from nonstick cookware, and
fire retardants) have been tied to an increased risk for ECHA InfoCard 100.000.713 (https://ech
celiac disease in young people.[9] DDE has also been a.europa.eu/substance-inf
shown to be present in increased concentrations in the ormation/-/substanceinfo/
tumors of patients with primary hyperparathyroidism.[10] 100.000.713)
KEGG C04596 (https://www.keg
Mechanism g.jp/entry/C04596)
PubChem CID 3035 (https://pubchem.nc
The biological mechanism for the thinning is not entirely
known, but it is believed that p,p'-DDE impairs the mother bi.nlm.nih.gov/compound/
bird's glands ability to excrete calcium carbonate onto the 3035)

developing egg.[7][11][12][13][14] Multiple mechanisms may UNII 4M7FS82U08 (https://pre

be at work, or different mechanisms may operate in cision.fda.gov/uniisearch/
different species.[7] Some studies have shown that srs/unii/4M7FS82U08)
although DDE levels have fallen dramatically, eggshell CompTox DTXSID9020374 (https://
thickness remains 10–12 percent thinner than before DDT Dashboard comptox.epa.gov/dashbo
was first used.[15] (EPA)
ard/chemical/details/DTX
Some studies have indicated that DDE is an endocrine SID9020374)
disruptor[16] and contributes to breast cancer, but more InChI [show]
recent studies provide strong evidence that there is no InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13
relationship between DDE exposure and breast cancer.[17] (14(17)18)10-3-7-12(16)8-4-10/h1-8H
What is more clear is that DDE is a weak androgen Key: UCNVFOCBFJOQAL-UHFFFAOYSA-N
receptor antagonist and can produce male genital tract
abnormalities.[18] InChI=1/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14
(17)18)10-3-7-12(16)8-4-10/h1-8H
Key: UCNVFOCBFJOQAL-UHFFFAOYAE
See also
SMILES [show]
Insecticide Clc2ccc(\C(=C(/Cl)Cl)c1ccc(Cl)cc1)cc2

Properties
References Chemical C14H8Cl4
1. ATSDR – Public Health Statement: DDT, DDE, and formula
DDD (https://wwwn.cdc.gov/TSP/PHS/PHSLanding.as Molar mass 318.02 g·mol−1
px?id=79&tid=20) Except where otherwise noted, data are
2. Walker, K. C.; Goette, M. B.; Batchelor, G. S. (1954). given for materials in their standard state (at
"Pesticide Residues in Foods, 25 °C [77 °F], 100 kPa).
Dichlorodiphenyltrichloroethane and verify (what is ?)
Dichlorodiphenyldichloroethylene Content in Prepared
Foods". Journal of Agricultural and Food Chemistry. 2 Infobox references
(20): 1034–1037. doi:10.1021/jf60040a006 (https://doi.
org/10.1021%2Fjf60040a006).
 3. Waliszewski, SM; Melo-Santiesteban, G; Villalobos-Pietrini, R; Gómez-Arroyo, S; Amador-Muñoz,
O; Herrero-Mercado, M; Carvajal, O (2009). "Breast milk excretion Kinetic of b-HCH, pp'DDE and
pp'DDT". Bull Environ Contam Toxicol. 83 (6): 869–73. doi:10.1007/s00128-009-9796-3 (https://do
i.org/10.1007%2Fs00128-009-9796-3). PMID 19551328 (https://pubmed.ncbi.nlm.nih.gov/195513
28). S2CID 24374271 (https://api.semanticscholar.org/CorpusID:24374271).
4. "NIST DDE MSDS" (https://web.archive.org/web/20200413072628/https://www-s.nist.gov/srmors/
msds/8467-MSDS.pdf?CFID=6441706&CFTOKEN=3aa7cf88111f43d5-7A960AA1-F2A1-B615-78
A041930E2DD768) (PDF). Archived from the original (https://www-s.nist.gov/srmors/msds/8467-M
SDS.pdf?CFID=6441706&CFTOKEN=3aa7cf88111f43d5-7A960AA1-F2A1-B615-78A041930E2D
D768) (PDF) on 2020-04-13. Retrieved 2015-04-30.
5. Stokstad, E (2007). "Species conservation. Can the bald eagle still soar after it is delisted?".
Science. 316 (5832): 1689–90. doi:10.1126/science.316.5832.1689 (https://doi.org/10.1126%2Fsc
ience.316.5832.1689). PMID 17588911 (https://pubmed.ncbi.nlm.nih.gov/17588911).
S2CID 5051469 (https://api.semanticscholar.org/CorpusID:5051469).
6. "Endangered and Threatened Wildlife and Plants; 12-Month Petition Finding and Proposed Rule
To Remove the Brown Pelican (Pelecanus occidentalis) From the Federal List of Endangered and
Threatened Wildlife; Proposed Rule," Fish and Wildlife Service, U.S. Department of the Interior,
February 20, 2008. 73 FR 9407 (https://www.federalregister.gov/citation/73-FR-9407)
7. ATSDR - Toxicological Profile: DDT, DDE, DDD (https://www.atsdr.cdc.gov/toxprofiledocs/index.ht
ml?id=81&tid=20)
8. "California Wild Spring 1994 – Peregrine Falcons" (https://archive.today/20070616194703/http://w
ww.calacademy.org/calwild/1994spring/stories/falcons.htm). Archived from the original (http://www.
calacademy.org/calwild/1994spring/stories/falcons.htm) on 2007-06-16. Retrieved 2007-03-21.
9. "Celiac disease linked to common chemical pollutants" (https://medicalxpress.com/news/2020-05-
celiac-disease-linked-common-chemical.html).
10. Hu, Xin; Saunders, Neil; Safley, Susan; Smith, Matthew Ryan; Liang, Yongliang; Tran, ViLinh;
Sharma, Joe; Jones, Dean P.; Weber, Collin J. (2021-01-01). "Environmental chemicals and
metabolic disruption in primary and secondary human parathyroid tumors" (https://www.ncbi.nlm.n
ih.gov/pmc/articles/PMC7845795). Surgery. 169 (1): 102–108. doi:10.1016/j.surg.2020.06.010 (htt
ps://doi.org/10.1016%2Fj.surg.2020.06.010). ISSN 0039-6060 (https://www.worldcat.org/issn/003
9-6060). PMC 7845795 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7845795).
PMID 32771296 (https://pubmed.ncbi.nlm.nih.gov/32771296).
11. Recovery Plan for the California Condor (https://ecos.fws.gov/docs/recovery_plans/1996/960425.
pdf), U.S. Fish and Wildlife Service, April 1996, page 23
12. "DDE concentration and percent eggshell thinning in Double-crested Conmorant eggs(North
Channel, Lake Huron, Ont.)" (https://web.archive.org/web/20070628141601/http://www.ec.gc.ca/s
oer-ree/English/Indicators/Issues/Toxic/Graphs/tx_s03_e.gif). Archived from the original (http://ww
w.ec.gc.ca/soer-ree/English/Indicators/Issues/Toxic/Graphs/tx_s03_e.gif) on 2007-06-28.
Retrieved 2009-04-15.
13. Guillette, Louis J. Jr. (2006). "Endocrine Disrupting Contaminants" (https://web.archive.org/web/20
090325085455/http://www.ehponline.org/members/2005/8045/8045.pdf) (PDF). Archived from the
original (http://www.ehponline.org/members/2005/8045/8045.pdf) (PDF) on 2009-03-25. Retrieved
2007-02-02.
14. Lundholm, C.E. (1997). "DDE-Induced eggshell thinning in birds". Comp Biochem Physiol C. 118
(2): 113–28. doi:10.1016/S0742-8413(97)00105-9 (https://doi.org/10.1016%2FS0742-8413%289
7%2900105-9). PMID 9490182 (https://pubmed.ncbi.nlm.nih.gov/9490182).
15. Division of Environmental Quality (https://www.fws.gov/contaminants/examples/AlaskaPeregrine.c
fm) Archived (https://web.archive.org/web/20080303174350/http://www.fws.gov/contaminants/exa
mples/AlaskaPeregrine.cfm) 2008-03-03 at the Wayback Machine
16. Chemical fact sheet: Organochlorine – The Breast Cancer Fund (http://www.breastcancerfund.org/
site/pp.asp?c=kwKXLdPaE&b=84567) Archived (https://web.archive.org/web/20061009104100/htt
p://www.breastcancerfund.org/site/pp.asp?c=kwKXLdPaE&b=84567) 2006-10-09 at the Wayback
Machine
17. Questions about Endocrine Disruptors (http://extoxnet.orst.edu/faqs/pesticide/endocrine.htm)
18. Longnecker, M. P.; Gladen, B. C.; Cupul-Uicab, L. A.; Romano-Riquer, S. P.; Weber, J.-P.; Chapin,
R. E.; Hernandez-Avila, M. (2007). "In utero exposure to the antiandrogen 1,1-dichloro-2,2-bis(p-
chlorophenyl)ethylene (DDE) in relation to anogenital distance in male newborns from Chiapas,
México" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1852527). American Journal of
Epidemiology. 165 (9): 1015–22. doi:10.1093/aje/kwk109 (https://doi.org/10.1093%2Faje%2Fkwk
109). PMC 1852527 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1852527). PMID 17272288
(https://pubmed.ncbi.nlm.nih.gov/17272288).

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